5-METHOXY-2-NITROPHENOL Chemical Properties

Melting point:

92-94 °C(lit.)

Boiling point:

298.4°C (rough estimate)

Density 

1.367

refractive index 

1.5830 (rough estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

6.95±0.13(Predicted)

form 

Powder or Crystals

color 

Yellow

CAS DataBase Reference

704-14-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29095000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

5-METHOXY-2-NITROPHENOL Usage And Synthesis

Chemical Properties

yellow crystals or powder

Uses

5-Methoxy-2-nitrophenol is a reagent in the synthesis of conformationally constrained spirocycles, which are used as CCR1 antagonists. 5-Methoxy-2-nitrophenol is also used in the preparation of phenylsulfonyl aminophenoxybenzoates which can serve as EP1 receptor antagonists.

Synthesis Reference(s)

Synthetic Communications, 23, p. 343, 1993 DOI: 10.1080/00397919308009786

Synthesis

The general procedure for the synthesis of 5-methoxy-2-nitrophenol from 2,4-dimethoxynitrobenzene was as follows: 2,4-dimethoxynitrobenzene (2.0 g, 10.9 mmol) was dissolved in 360 mL of dichloromethane and cooled to 0 °C. Subsequently, anhydrous aluminum trichloride (2.91 g, 21.3 mmol) was added in batches. The reaction mixture was heated to reflux and kept for 5.5 hours (the color of the reaction solution changed to bright red). After completion of the reaction, it was cooled to room temperature and 10% aqueous hydrochloric acid solution was added slowly and dropwise. The mixture was extracted three times with dichloromethane. The organic layers were combined and dried with anhydrous magnesium sulfate. After concentration under reduced pressure to remove the solvent, the crude product was purified by column chromatography (cyclohexane/ethyl acetate = 10:1) to afford 5-methoxy-2-nitrophenol (11) as a yellow solid (1.64 g, 9.69 mmol, 89% yield).

References

[1] Synthetic Communications, 2009, vol. 39, # 11, p. 2053 - 2057
[2] Synlett, 2015, vol. 26, # 10, p. 1395 - 1397

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